2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine TCI M3186

Chemical Identity

CAS No.: 408502-23-8
PubChem: CID 44754862·SID 468592323
Formula: C12H18BNO3
Molecular weight: 235.09 g/mol
Purity: >98.0%(GC)(T)

Full identifiers (IUPAC, SMILES, InChIKey)

IUPAC: 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine
SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=NC=C2)OC
InChIKey: RLHAGSICYJAHMN-UHFFFAOYSA-N

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2-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, CAS 408502-23-8, is a heterocyclic building block supplied by TCI. Structurally, it is a pinacol boronate ester attached at the 4-position of a pyridine ring, while a methoxy group occupies the 2-position. Its primary role in the laboratory is to serve as the boron partner in Suzuki-Miyaura cross-coupling reactions, one of the most widely used methods for forming carbon-carbon bonds in modern organic synthesis. Using this reagent, researchers can install a methoxypyridine fragment directly onto another aromatic or heteroaromatic framework in an efficient manner.

The advantage of the pinacol boronate ester form over the corresponding free boronic acid lies in its generally better storage and handling stability, because the ester does not readily form the cyclic anhydrides or boroxines that complicate stoichiometric weighing. A clearly defined solid makes milligram-scale weighing far more reliable, which matters a great deal when a coupling is run on small quantities of a precious intermediate. In addition, the electron-deficient character of the pyridine ring often makes coupling reactions difficult, so having a ready-to-use pyridyl boron reagent on hand saves researchers considerable time.

In Indonesian laboratories, this building block is typically used in university and institutional synthetic organic chemistry groups, in medicinal chemistry and drug discovery programmes, and in materials research where heteroaromatic fragments must be joined together. The methoxy group at the 2-position can also serve as a point for further modification, giving the molecule value as an intermediate that can be elaborated in later synthetic steps rather than only as a terminal coupling partner.

Related TCI products

Suzuki-Miyaura cross-coupling — the reagent acts as the boron partner that transfers the methoxypyridyl fragment to an aryl or heteroaryl halide under palladium catalysis.
Medicinal chemistry library synthesis — methoxypyridine motifs are common in bioactive scaffolds, and a ready-to-use boron reagent lets chemists diversify a core structure quickly.
Heteroaromatic scaffold construction — the reagent joins an electron-deficient pyridine ring to other aromatic systems, a bond formation that is otherwise troublesome to achieve.
Milligram-scale exploratory synthesis — the well-defined solid form allows confident stoichiometric weighing when only small amounts of a valuable coupling partner are available.
Multi-step intermediate preparation — the 2-methoxy group provides a handle for subsequent modification, so coupled products can be elaborated further in downstream steps.

Brand	TCI (Tokyo Chemical Industry)
CAS number	408502-23-8
Molecular formula	—
Purity	—
Category	Chemistry > Building Blocks > Heterocyclic Building Blocks
Pack sizes	Please refer to the catalogue listing for available package sizes
Physical form	Solid
Storage	Store in a tightly closed container in a cool, dry place

Chemical class: Pinacol boronate ester of a substituted pyridine

Store the container tightly closed in a cool, dry, well-ventilated area, away from moisture and from direct sunlight. Boronate esters are best kept in their original supplier bottle or in a tightly sealed amber glass container, and many laboratories prefer to store them under an inert atmosphere to limit exposure to air and humidity. Handle the solid in a fume hood using gloves, safety glasses, and a laboratory coat, and weigh it carefully to avoid generating dust. Keep the material away from strong oxidising agents. Always consult the manufacturer's Safety Data Sheet before use, and dispose of residues and contaminated materials in accordance with your institution's chemical waste procedures.

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